


Stiles is a dumbass

by Herlilacskies



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Daddy Kink, First Time, First Time Bottoming, M/M, Oral Sex, Stackson Brotp
Language: English
Status: Completed
Published: 2020-05-05
Updated: 2020-05-05
Packaged: 2021-03-03 05:07:56
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 6,430
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24019513
Author URL: https://archiveofourown.org/users/Herlilacskies/pseuds/Herlilacskies
Summary: Stiles realizes Jackson is totally his best friend and then it just devolves into sex from there, basically. Sex between Stiles and Derek, to be clear.
Relationships: Derek Hale/Stiles Stilinski, Stiles Stilinski & Jackson Whittemore
Comments: 2
Kudos: 117





	Stiles is a dumbass

**Author's Note:**

> This is a terrible vulgarity.  
> I urge you to continue at your own discretion.  
> It's basically all porn. I started writing it as, you know, Stackson Brotp, but then it kind of just—sex.  
> Stiles has a Daddy kink? He's the Daddy, I guess.  
> I can't believe I just wrote six thousand words of smut.

Were Stiles and Jackson friends? Stiles didn’t know either, he’d just barely realized it. One day he was immediately calling Scott about absolutely nothing and now he was calling Jackson whenever he got bored of the researching. When had Scott stopped being his best friend?

So as Stiles would do, in a panic, he dialed up Derek because Stiles hadn’t quite been friend-zoned by the literal adonis so he was going to share all of his problems with the man until he told him to fuck off and die or engage in sexual and/or romantic relations. It could go either way and Stiles would probably be happy either as long as Derek was happy and wasn’t that the most grown-up shit he’d ever thought.

“ _ What is it _ ,” Derek grumbled from the speaker, his voice sleep-heavy, and goddamn arousing. Stiles was utterly fucked over this man.

“I think Jackson...and I...I think—”

“ _S_ _ tiles, I really don’t want to hear this. I’m going back to bed _ .” Then the call ended.

Stiles stared at his phone, a devastating calm settling over him, his chest tightening painfully. That was Derek telling him to fuck off and die. He immediately scrolled down to  _ Whittemore _ and laughed wetly and bitterly as he called him.

“ _ What _ ,” the teen asked, drowsy.

“Derek doesn’t want me. I mean,” he said, wiping at his tear-filled eyes, “I knew that, of course, I knew that. I just…I just...I don’t think I’d realized that he  _ actually  _ doesn’t want me until now.”

“ _ Shut up _ ,” he grouched. “ _ Anyone who has seen you guys together knows how much you both want each other. I don’t understand why that idiot hasn’t done anything yet _ .”

“He did. He told me to fuck off and die, Jackson. He just did and I’m trying to accept that,” he said, nearly sobbing, his voice shaking.

“ _ Wait, he said  _ what,” Jackson growled through the receiver.

“NO—no. Not literally, just in his own way, he made himself clear,” he said, only a little shaky by the end.

“ _ So you’re crying because Derek is an emotionally stunted asshole who can’t express his feelings properly. What did he say? Exactly, Stiles _ .”

“Well,” he sniffed, “I was calling him, t—trying to work something out and—and he just said he didn’t wanna hear it.” He wiped at his tears and wished that he hadn’t fallen so hard for the man, he knew Derek would never see him like that.

Jackson was silent for several seconds.

“Jackson,” Stiles questioned, hesitantly, wondering if he’d driven him away too. Why did he always have to push his problems onto other people? He was so anno—

“ _ Yeah, no, I was...What did you say _ ,” he asked. “ _ Before, what were you trying to tell him _ .”

“That me and you...were friends. I realized we’re like...best friends. I haven’t hung out with Scott in like...three months.”

After a few seconds, Jackson said, “ _ You started like that, didn’t you? The ‘Jackson and I’ bit? A long pause after? That’s when he stopped you _ .” The last part wasn’t even a question and now Jackson was sounding all fucking smug.

“Why,” Stiles questioned, hesitant, but mostly petulant. “What does it matter how I said it?”

“ _ Derek thinks we’re fucking _ .”

Stiles made a strangled noise. “What,” he squeaked.

“ _ You gave him the impression that  _ you and I _...are together _ ,” he stated.

Stiles took in a sharp breath as his eyes widened slightly. “Oh no, did I?”

“ _ Yes. I’m going back to sleep now _ .”

“Wait, wait, wait,” he said. “What if he really did just have enough of my shit, Jackson? What if—”

“ _ Stiles. Shut the fuck up _ .”

“Fuck you,” he said, quick.

“ _ No, fuck you _ ,” Jackson threw back.

“No, fuck  _ you _ ,” Stiles reiterated.

There was a moment of silence. Then Jackson said, “ _ Stiles. Call Derek. Right now _ .”

“But—”

“ _ Hang up the phone and  _ call  _ him _ .  _ Tell him you wanna fuck and that your dad’s at work _ .” Then he hung up.

“Oh my  _ god _ ,” Stiles said, scandalized, face heating up, completely mortified at the prospect of even—He found himself scrolling back up to Derek’s name in a matter of milliseconds, regardless of his blotchy cheeks.

Derek didn’t answer. Not the first time or the second or even the seventh, but Stiles persisted and on the twelfth dial, Derek surprisingly picked up—angry.

“ _ What the hell _ ,” he growled all hot and gravelly.

“My dad’s at work,” he rushed out in one breath. Before Derek could interrupt he spit out, “I want to have—sexual—intercourse—With you!” By the end, he was shouting at his ceiling because he was an awkward person sometimes—mainly with Derek.

Derek was silent after Stiles’ outburst.

“D—Derek,” Stiles asked, his heart in his throat. He was on edge.

“ _ Um _ .”

“Um what, Derek,” Stiles almost screamed into the phone.

“ _ I—uh—Stiles...you’re seventeen _ .”

“ _ Derek _ ,” Stiles whined, petulantly. Now he really did want to have sex, but that wasn’t even the point. Why was Derek so cruel? There were so many mixed messages. “You want me?” he asked, miserably.

“ _ I— _ Stiles,” he said.

“ _ Derek _ ,” Stiles cried feebly, desperate and pitiful.

“ _ You’re  _ seventeen,” he reiterated, sounding overwhelmed.

“Derek,” Stiles gritted out. “Do—you—want—me,” he enunciated.

“ _ Stiles _ ,” he said lowly, “ _ I want more than sex _ .”

“Oh,” Stiles breathed, elation slowly crawling through him. “Oh,” he said again, louder this time. “So are you gonna come over,” Stiles asked, earlier doubts completely forgotten.

“ _ I’m hanging up _ ,” Derek said.

“No, wait,” he shouted, cringing at the volume. “We don’t have to... _ have sex _ ,” he whispered. “Cuddle me,” he asked.

“ _ Stiles _ ,” Derek said reluctantly.

“Derek, my dad thought me and Malia were fucking like...two years ago. So come over. Or I’ll come over there.” He huffed at the end, hoping he at least sounded a little threatening. “I am not above doing that,” he admitted lastly.

“ _ We are _ not  _ having sex and you are _ go _ ing to tell your father about this in the morning _ .”

“So you’ll come over,” Stiles asked, but not really asked in that way that you want to ask, but don’t.

“ _ Stiles _ .”

“ _ Derek _ .”

After a few silent moments, Derek grit out, “O _ K _ .”

“OK? OK! OK, great.” After an awkward moment of silence, Stiles added, “Um...I don’t—Uh...know...what to do...now.”

“ _ I’m hanging up _ ,” he said.

“B—But, Derek.”

Silence. “ _ I am hanging up and driving over, OK _ ?”

Silence. “OK,” Stiles drew out, reluctant. Then Derek hung up. Stiles pulled the phone away, frowning slightly, “Well that was abrupt.” He switched over to text and typed out:  _ HE’S COMING  _ OVER.

After a few minutes, his phone lit up with an incoming text:  _ Get that werewolf dick _ .

Stiles sucked in a sharp breath as he felt his cheeks flame and he immediately sent:  _ Jesus _ fuck _. He’s coming over to  _ cuddle  _ me. _

_ Vanilla _ , is all Stiles got in reply. Douchebag.

After a short while, Stiles heard Derek’s car pull up and he started to feel a little tingly, a little anxious. Stiles sat on the edge of his bed, room dark and his phone forgotten at his side.

“Why are all the lights off,” Derek asked, walking into Stiles’ room and walking toward the computer desk, turning on the overhead light, mostly for Stiles’ benefit.

“It’s like two in the morning, Derek.”

“Yes,” he said, nodding and surveying the room. “But it’s also you.”

“Shut up and cuddle me,” Stiles said, feeling a  _ little _ shakey. He quickly looked anywhere else when Derek looked his way, eyes dropping to the floor.

Derek eyed Stiles, “Uh-huh.” After a moment, Derek walked over and settled next to Stiles. “Stiles. What are you doing?”

“What do you mean,” Stiles shrugged, still looking at the floor, fingers itching to do something, anything really.

“Stiles...we are constantly all over each other. Why are you suddenly more strange now?”

“Well, now it’s serious,” Stiles said.

“Stiles, if you’re not ready—”

“I am,” Stiles said, voice raised as he abruptly got up and took off his shirt. Oh, Jesus, why’d he take his shirt off? Then he proceeded to push down his sweats and slide under the covers as quickly as he could. “Now cuddle me.” He felt like he was going to start sweating. Shit, maybe he was.

“Stiles,” Derek said, kicking off his shoes and pulling off his shirt, “just pretend like we’re platonically cuddling and that you didn’t ask me to fuck you.”

“Oh my god,  _ Derek _ ,” he said, pulling the blanket over his face. “What the fuck?” Stiles felt the bed dip and nearly had a heart attack, just barely withholding the involuntary noises from leaving his throat.

Derek pulled the blanket away from Stiles’ face and he was so  _ so _ close and Stiles thought his chest might burst out of his chest at the rate it was going. Then Derek’s lips were on his and he was melting, he was sure of it. Too soon the man was pulling away and Stiles was chasing after him, slightly dazed.

“Um,” Stiles muttered stupidly. Hesitant, he asked, “Can we—Can we do that again?”

Derek smiled, nodding as he leaned down again. Stiles hesitantly brought his hands up, finding himself clinging to Derek’s biceps and then finding his way to Derek’s back as he bracketed his legs on either side of one of Stiles’ legs. Stiles was panting when Derek pulled away, only to start at his jaw and down to his throat. Wet, hot, suction that made Stiles  _ want, _ and when Derek bit into the base of his throat, he let out a high-pitched mewl which had him panicking in embarrassment and trying to push Derek away. The man only sunk lower, keeping Stiles under him as he dropped his forehead to Stiles’ throat.

“We’re not having sex,” Derek said.

“We aren’t,” Stiles said, his heart beating a mile a minute.

“We aren’t,” Derek said feebly.

“Nope,” he squeaked when he felt Derek’s bulge press into his thigh. Jesus, Derek was going to kill him.

“What time does your dad’s shift end,” he asked, snuffling into Stiles’ throat as he surreptitiously ground down against Stiles’ thigh.

“Six,” he muttered, adding, “maybe? Probably—” He groaned. “I cannot think, Derek, with you—Jesus!” he shouted as Derek bit into the juncture between Stiles’ neck and shoulder with blunt teeth. “You’re gonna kill me,” Stiles panted out.

“Maybe,” Derek said lowly, dragging his nose up his throat and behind his ear, then back down. He laved over and sucked on Stiles’ pronounced clavicle bones, making Stiles’ heart stutter, but it was only a pit stop on his way down.

Stiles’ hands fisted into the sheets when he felt something hot and wet on his nipple. “Move  _ on _ ,” Stiles found himself whining moments later, which caused Derek to bite down and Stiles to gasp out in surprise. He realized he was getting less and less embarrassed the lower Derek got, hands twitching at his sides.

Eventually, Derek was at the hem of his boxers and looking up with an unreadable expression, barely illuminated by the light. Stiles nodded. Then Derek was pulling Stiles’ boxers down and Stiles was lifting to help out. Then Derek’s mouth was hovering over Stiles’ dick and abruptly sucking the head into his mouth. Stiles had only ever had his hands and his fingers so a mouth on his dick was definitely going to ruin his own hand for him.

Derek mouthed and sucked at his cock, one hand stroking where his mouth couldn’t reach, the other playing with his balls. Stiles was not going to last. “Derek, Derek,  _ Derek _ ,” he panted. Derek’s mouth came off with a  _ pop _ and then it was just his hand, his thumb swirling around his tip, making Stiles delirious with need. Then Derek’s hand on his balls disappeared and his mouth was suddenly sucking his sac into his mouth and Stiles shouted, “Derek—Fuck!” Why was that so hot? He wasn’t even shaved. He pointedly did not think about that and let the pleasure steal all his thoughts. Derek started nipping at his balls and then he was laving his tongue down Stiles’ perineum and licking over his hole, which had Stiles cumming with Derek’s name on his lips.

Stiles lay there, dazed and wistfully wishing he’d been able to cum on Derek’s cock. Feel Derek’s cock push inside his tight hole. “I need your cock inside of me, Derek.”

“Next time,” he promised.

Stiles looked up to where Derek was lazily licking the cum from his own fingers and Stiles’ spent cock. He shuddered at the sight and whined, “But Derek, you still have to cum.” He tried, “I have lube?”

Derek smiled, but it was all teeth. “Next time.” Then he pulled his boxer-briefs down until he could hook them under his large and hairy balls. Stiles’ mouth watered and he was kind of scared.

“I—That’s too big,” Stiles said. “I can’t fit—That won’t—” He shook his head because he was so full of want, but also panic because Derek’s dick was the epitome of a fucking monster cock. It had to have been  _ at least _ seven or eight inches in length, which probably wouldn’t have been so bad, but the fucking girth, it had to be at least— _ at least _ seven inches around and fuck that was super hot but made him want to hide his hole from Derek. His very tight and  _ untouched _ hole. Derek was going to fucking wreck him and Stiles wasn’t sure he would stop him.

“Stiles, calm down.” He looked concerned and Stiles wasn’t going to wave it away because  _ he _ was concerned about getting ripped open his first time. He looked accusingly at Derek’s cock. “Stiles, I don’t have to top.”

Then Stiles looked at Derek accusingly, like he was trying to steal Stiles’ fucking candy. “I didn’t say I don’t want the  _ thing _ ,” he looked at Derek’s dick pointedly, “in me, I just—I’m not quite sure it will even fit in there.” He stared at Derek’s cock, calculating eyes studying the length. It was dripping precum onto Stiles’ stomach and Stiles could feel his own dick twitching. “Maybe you should fist me before you try and put your dick in me,” Stiles idly wondered aloud, studying the monster dick, his mouth salivating.

Derek stared at him, very unsure. “So...you don’t want to fuck me,” he surmised warily.

Stiles glared accusingly once more. “Did I say that, Derek? Did I say I don’t want my dick inside your glorious ass?”

Derek’s cheeks colored. “N—No,” he stuttered out.

“Good then.” His eyes fell back to Derek’s dick, then, face apprehensive and calculating. “So,” he said after a moment, “can I?” He gestured to the thick cock hanging between them, licking his reddened lips absently.

“Can you what,” Derek asked.

“Can I touch you,” Stiles clarified, exasperated. “I’d love to suck you off, man, but I mean—I’m not even sure I could fit that thing in my mouth.” He tilted his head slightly and gave Derek’s cock-head a quizzical look.

“Please stop looking at my dick like that.”

“Like what,” Stiles said, licking his bottom lip.

“Like your,” he struggled momentarily, “sizing it up,” he finished with an air of frustration.

Stiles smirked, eyeing his dick again. “Well, I am sizing it up, Derek. But I don’t see a problem, you’re still hard and I still want your dick in my mouth—however much I can fit,” he amended lastly.

“Stiles,” Derek intoned.

“You’re gonna face fuck me one day,” Stiles promised. The thought of Derek suffocating Stiles with his cock and cumming down his throat in hot spurts had a low moan slipping out. “OK,” Stiles said, breath heavy. “Get on your back.”

“Stiles,” he said, low and thick with arousal.

Stiles shot up and they kissed, but it was hungrier and more desperate than it had been earlier. He pushed at Derek’s boxer-briefs, getting them mid-thigh before Derek was pulling away briefly to get the dastardly cloth the rest of the way off. Then they were sucking face once more and Stiles had a hand wrapped around Derek’s dick, his fingers barely meeting, the other hand gripping the back of Derek’s neck, deepening the raw bruising kiss. Derek moaned into his mouth and Stiles moved his lips to his jaw, biting and mouthing at his stubble, telling him to get on his back. The hand around his cock squeezed and Derek started to helplessly fuck up into Stiles’ fist, jabbing Stiles’ hipbone with every thrust. Stiles found it incredibly daunting, but overwhelmingly obscene.

“God, Derek, you’re so perfect,” he growled low into the underside of the older man’s jaw as he laid down. Stiles’ grip tightened and Derek let out a whimpering mewl that had Stiles biting just behind Derek’s ear and whispering, “Sound so good, so hot.”

“Stiles,” he moaned, hips bucking up and brushing against Stiles’ cock.

He hissed at the oversensitivity and tightened his hold on Derek’s cock almost painfully. Derek whimpered and stilled while Stiles sucked a bruise into the base of his throat. “So good for me, Der.” He stroked the man’s cock and sucked at his clavicles, mumbling, “So soft.” He bit at the bone as the hand on Derek’s neck was dragged down to his chest, running his fingers through the hair there that felt less coarse than Stiles had expected. “So hairy,” he said into the shallow valley of Derek’s collarbones.

“Stiles,” Derek moaned, almost whining, his hips shifting, but not thrusting.

“‘S OK,” Stiles mumbled, his face coming back up to Derek’s and pulling his bottom lip between his teeth and pulling, then sucking obscenely. “Gonna take care of you,” Stiles breathed against Derek’s lips as the older man panted against his mouth. Then he pulled away and shifted backward until he could settle down between Derek’s legs so he could lick his cock.

“Stiles,” Derek urged, panting, his cock red and weeping, throbbing against Stiles’ hold.

Stiles had one hand wrapped around Derek’s thigh and rubbed at the soft skin of his inner thigh, saying, “Don’t worry, Daddy’s got you.” Stiles’ eyes darted up to Derek’s face, hand stilling at the base of the man’s cock and his other fingers tapping out an odd pattern on his inner thigh. Had he misstepped?

“Stiles,” Derek whimpered, fresh precum dribbling over the head of his cock, his eyes half-lidded and solely focused on Stiles’ face.

Stiles asked, “OK,” his voice a little shaky, grip tightening around Derek’s cock minutely.

Derek whimpered, nodding frantically. “Yes, yes, Daddy.  _ Please _ .”

A thrill went through Stiles at the name and he could feel himself getting hard again at the mere utterance of it. Stiles smiled and lifted his head from Derek’s thigh, nuzzling at the crease of his leg and nipping at the soft skin there. Derek’s hips made abortive thrusts and Stiles tightened his hold around the girthy member.

“ _ Daddy _ ,” Derek whined, eyes flashing briefly.

“Come on,” Stiles said, licking up the length of Derek’s cock. “Let go for Daddy. Wanna see you lose control,” he said, swirling his tongue at the tip and sucking the massive head into his mouth. His asshole certainly wasn’t as big as his mouth.

“ _ Stiles _ ,” Derek whined. Stiles tsked and tightened his grip painfully. “Sti—” Derek’s chest seized upward abortively. “Daddy,” he whimpered, a visage of confused lust.

“That’s it, baby, Daddy’s got you.” He stroked Derek in apology, sucking and licking the tip of his cock. “Gonna make you feel real good, baby boy.” Stiles flicked his eyes up to gauge Derek’s reaction.

“ _ Daddy _ ,” he urged.

“‘S OK,” he mumbled against Derek’s dick. He let his mouth slide down the considerable member and slobber around it, slicking it up so it wasn’t so dry. Stiles brought the hand wrapped around Derek’s thigh to his balls as he stroked Derek and put as much cock into his mouth as he could. He barely got half down his throat—because it was so fucking wide—before it was painful and almost suffocating. He pulled off, gasping as he laved his tongue over the head, his hand using the slobber to ease the slide. He dragged his wet lips down the length of his cock and mouth at the base as one hand stroked his member and thumbed the head, his other hand trailed a finger down Derek’s perineum.

Derek moaned and then whined, “ _ Daddy _ .” His fists were clenched around the sheets, eyes half-lidded and crimson, mouth parted and panting, his fangs on full display. Stiles’ skin heated up, mouth parting on a moan as he wrapped his lips around Derek’s cock head once more, a finger rubbing between his hairy asscheeks. Derek moaned and bucked, getting at least another inch or more inside of Stiles’ mouth and successfully cutting off all air. Then he came down Stiles’ throat, flooding his cavity with too much cum. Tears sprung as Stiles convulsed and desperately tried to dislodge the thick head from his throat, cum and spit at the side of his mouth. His eyes were bulging and his nose was buried in the dark curls at the base of Derek’s dick.

Stiles frantically braced both hands on Derek’s pelvis and pulled off with a wet gasp, coughing and trying to swallow the rest of the cum that hadn’t already slid down his throat or Derek’s dick. Derek’s dick flopped against his stomach and Stiles glared at it before flicking his glare to Derek’s blissed-out face.

“Yeah,” Stiles questioned, “good for you?” Derek wasn’t even on this planet. “Well, it’s gonna get better.” He rubbed his index finger in the mess that’d come out of Stiles’ mouth and pushed one cheek aside so he could press his finger against the werewolf’s rim. Then he abruptly pushed it inside past the knuckle until his entire finger was seated in the heat of his hole. He didn’t even give a shit he was so angry, but still fucking aroused.

Derek grunted and blinked blearily down at him. “S—Stiles,” he mumbled, brows pinched.

Stiles smacked his inner thigh hard. “Nope.” Then he went back to Derek’s hole and pulled the digit out halfway before pushing it back in.

Derek let out a punched-out groan, scrabbling for purchase at the rumpled sheets. “ _ Stiles. _ ”

Stiles smacked him again, harder, the sound resounding throughout the room. “No,” he said, voice low and rough with anger and lust. He pulled his finger free fully and rubbed two fingers through the mess on Derek’s stomach. Then there were two fingers curling inside Derek’s ass. He pulled his fingers out and scooped up what was left of the mess and smeared it all over Derek’s hairy chest because he was still fucking pissed and an asshole. Then he sat back on his knees and reached over Derek and into his nightstand drawer, pulling out an almost empty bottle of lube—he wasn’t that much of an asshole.

“Daddy,” Derek whispered, one hand tugging at the wrist braced on the bed by the older man’s shoulder.

Stiles pulled back and smiled as he looked down at him, dislodging Derek’s feeble hold on his wrist to cup his cheek, his thumb rubbing absently. There were tears in his eyes and Stiles was kind of concerned. “What is it, baby boy?” Derek’s eyes darted, searching, and Stiles desperately wanted him to say what was wrong. His grip tightened on Derek’s face, “Derek, what’s wrong?”

Derek’s eyes widened minutely and he shook his head. “N—Nothing, Daddy. Just—Just kiss me.” He wound his hand around Stiles’ wrist again and licked his lips, adding, “Please, Daddy.”

Stiles smiled and slid his hand down to grip the back of Derek’s head, his hand gripping Stiles’ bicep and squeezing as he sucked Derek’s bottom lip between his own lips. He tilted Derek’s head slightly, deepening the kiss. After a few moments, Derek’s hand slowly slid back down to Stiles’ wrist and took hold, dragging it down his body and lower until he was pushing it insistently towards his ass. Stiles smirked into the kisses as they tapered off.

“Is that where my baby boy wants his daddy,” Stiles teased, nuzzling Derek’s cheek and mouthing at the corner of his mouth.

Derek nodded frantically, mouthing against Stiles’ bottom lip and panting. “Yes, Daddy, please.”

Stiles pulled back. “Yeah, baby? Want me to fuck you with my fingers?”

Derek nodded, brows pinched. “Please, Daddy. Need you.”

Stiles smiled, leaning down, and kissed him one last time. Then he pulled away just enough so he could dig his teeth into Derek’s bottom lip. He whimpered and Stiles licked across his flushed lip one last time before pulling away with a grin. Derek whimpered and Stiles said, “You want Daddy at your hole, don’t you baby?” Derek nodded with a small frown. Stiles brought his hand back up and pushed a corner of his mouth upward. “Daddy’s gonna make you feel good, OK, baby? You want Daddy to make you feel good?”

Derek nodded, “Yes, Daddy.”

“Good,” Stiles smiled. He shifted further down the bed and sat back on his knees, pulling Derek’s asscheek to the side to look at his hairy hole. After a moment, he looked back up to Derek’s hazel-green eyes with a mischievous glint in his own. “Hey, want Daddy’s to eat you out?”

Derek’s brows came down in what seemed to be discomfort. “I—I don’t know, S—Daddy. It’s dirty down there.”

He put a hand on Derek’s knee and rubbed his thumb back and forth. “Derek, I don’t care that shit came out of your ass.”

“Stiles,” he said, affronted.

Stiles smacked Derek’s inner thigh with the back of his right hand and said, “Really, Derek. I mean, you tell me to lick a door handle, I’d probably do it. For money. I’d probably do just about anything for twenty bucks.” He nodded, thinking about crazy shit.

“Stiles.” Stiles smacked him again, harder. “Daddy,” he corrected, a fond smile on his lips. After a moment, he said. “OK, then. But please don’t lick weird shit for twenty dollars.”

“I’d probably let you suffocate me with your dick again for fifty,” he said.

“Fifty,” Derek questioned, an amused lilt to the corner of his lips.

“Fifty,” Stiles said definitively with a light smack to Derek’s thigh again. “I’m still pissed at you.”

“Please don’t be mad at me, Daddy.” Stiles groaned. “What is it, Daddy?” Derek was smirking now.

“Fuck you,” Stiles said.

“Please, Daddy, will you?”

Stiles shifted further back and slapped Derek’s thigh once more. “Turn around, get on your knees, ass in the air, baby.”

“Yes, Daddy.”

Stiles shook his head, fondly exasperated. “Hurry up, you ass.”

Derek turned over and settled on his knees with his ass in the air, his face buried in Stiles’ pillow.

Stiles scooted closer, setting the bottle of lube by Derek’s leg, and bringing his hands up to pull Derek’s cheeks apart. Then he pushed them back together for the hell of it because he could. He kneaded the harry globes and littered bites all over, prodding Derek’s hairy asshole with the tip of his tongue every now and again.

“Daddy,” Derek whined, pushing back. Stiles pulled back and slapped Derek’s ass. “Daddy,” Derek gasped. “Please, Daddy. Stop teasing.” Stiles smirked and pulled Derek’s cheeks apart once more, blowing on his hole. “Da— _ Daddy _ ,” Derek gasped as Stiles swiped his tongue over his hole.

“Yeah, baby, like Daddy’s tongue on your hole?” He licked from Derek’s balls up to the crack of his ass and back down to swirl the hairs around his hole. Then Stiles started pushing at the ring of muscles, Derek letting out low moans as he tried to hold his ass in place and not push back.

“Yeah, Daddy,” he panted against his folded arms. “Please, Daddy, wanna cum on your cock.”

Stiles hummed against Derek’s hole, licking and sucking at his puffy rim. He flattened his tongue and pressed hard, sucking at the skin. He pulled back and grabbed the bottle of lube, then he went back and rested the side of his face on Derek’s ass so he could mouth at his wet hole while he uncapped the lube.

“Daddy,” Derek urged, pleading.

“Yeah, yeah,” he mumbled against his flushed rim. “Baby boy’s impatient, isn’t he?” Once he had the bottle open, he pulled away once more to slather two fingers in lube. He nudged a cheek slightly and swirled his finger around the rim before sinking both fingers in alongside one another.

“ _ Sti—Daddy _ ,” Derek gasped out, panting. Derek’s brows were pinched. “Wait, wait, wait. St—Daddy, stop.”

Stiles pulled his fingers out immediately. “What is it, baby?” Derek buried his face in his arms and Stiles’ pillow, the tips of his ears reddening. “Derek, use your words.”

“It feels like—weird,” he finished lamely, miserable.

“We—Oh my, God,” Stiles said, astonished. “Derek, are you—Is this your first time? Was that why you were so weird earlier?” Derek nodded mutely. Stiles dropped down to Derek’s side so he could face him and said, “Look at me, baby.” When Derek turned around, Stiles said, “You know it’s OK that you’ve never done this right? You know I’ve never done this so it’s fine. OK?”

Derek nodded. “OK, Daddy.” Stiles smiled and kissed him chastely.

Then he pulled away. “So can I put my fingers inside of you again?”

“Yes, Daddy. I want you inside me.”

Stiles huffed in amusement and kissed him on the cheek. “Yeah, yeah,” he said coming back and settling between Derek’s legs. He slid two fingers in all at once. “You talk like you’ve had plenty of dick before me.”

“ _ Stiles _ ,” Derek groaned

Stiles smacked his ass in reprimand and began pulling his fingers out lazily and pushing them back in just as slowly, curling them inside and looking for a bundle of nerves. Stiles’ fingers were long so he obviously knew where his own was, but he’d never been inside of Derek.

“Hey,” Stiles said, “since you’ve never been fingered and therefore never stimulated your prostate when I find it—and I will—you might feel like you gotta piss, but you probably won’t.”

“What do you mean ‘probably’,” he questioned, panicked. “And I thought you were a virgin,” he said accusingly.

Stiles pulled his fingers out and grabbed the bottle to slick up three this time. “Just ‘cause someone’s never given or received doesn’t mean they’ve never stolen KY jelly and fucked themselves with their fingers until they’d found their prostate and fucking abused it. OK?”

Derek nodded dumbly. After a moment, he said, “Please don’t abuse my prostate, Daddy.”

“Hey, I’m not a pedophile for calling you ‘baby boy’, am I,” Stiles questioned abruptly.

“No, Stiles, Jesus.”

Stiles smacked him just because this time. “What? How am I supposed to know, there is very little porn with explicit Daddy kinks, OK? Sue me.”

“If you were a pedophile you would not have your fingers up my ass.”

“They’re not in your ass yet,” Stiles grumbled.

“They were, and your tongue was on my ass, oh, and you were choking on my cock too—”

Derek’s head shot up and his mouth parted on a punched-out moan as Stiles shoved three of his fingers in abruptly, essentially cutting off Derek’s stream of bullshit. “How do you like that,  _ baby boy _ ?”

“Cum—in my ass—Daddy,” Derek panted out before dropping his head back to his arms and the pillow.

Stiles crooked his fingers, searching for his elusive prostate. “Now you’re just saying obscene shit to get Daddy aroused.”

“Daddy,  _ make me cum _ ,” Derek shouted the last part and his body shuddered, his knees going week.

Stiles patted Derek’s hip soothingly and rubbed gently at his prostate. “Found it,” he grinned. “Gonna lift up for Daddy,” he asked.

“I—I can’t, Daddy.” He added, his voice shaking, “It’s t—too much. Please, Daddy.”

Stiles remembered how intense his first prostate orgasm had been and wondered if it all was too much too fast. Stiles had been fingering himself since he was in middle school whereas Derek had just had a finger inside of himself for the first time only a few moments ago. He pulled his fingers out and leaned over Derek, resting his temple against Derek’s triskelion tattoo. “Derek, if it really is too much, we can stop. All of it.”

“ _ Stiles _ ,” Derek whined. Stiles waited patiently, trailing a slick finger over the lines of his tattoo. After several long moments, of heavy breaths, Derek said, “Please, don’t stop, Daddy.”

Stiles smiled and kissed Derek’s spine as he got up. “You got it, baby boy.” He didn’t bother trying to make Derek hold his ass up and slipped three fingers back inside. He’ll mercilessly abuse Derek’s prostate one day soon, but for now, he’ll settle for easing him into ass play.

When Derek started to push back and let out filthy and obscene moans, whimpering, “Daddy,” Stiles decided he needed to put his dick in Derek’s hole.

Stiles pulled his fingers out and said, “Daddy’s gonna fuck you now, OK, baby?” Stiles lifted Derek’s leg so he could pull his together and then Stiles could Straddle the back of his thighs and slide into him that way.

“Please, Daddy,” he whimpered into Stiles’ pillow. “Want you to cum in me, Daddy. Make my hole sloppy.”

“Jesus, fuck,” Stiles said, moving Derek’s other leg and straddling his thighs, frantically scrabbling for the lube. “You’re so fucking hot, baby boy. Fuck. I’m gonna make you come on my fingers next time.”

“ _ Daddy _ ,” Derek let out a high keen. “Want you so bad,” he panted, pushing back.

“Yeah, baby,” he said, finally finding the bottle and squirting some onto his cock, slathering it all over because one can never have too much lube. Maybe, but it’s worked so far for Stiles. “Gonna fill you up so good, baby boy.”

“Please, Daddy. Please, need you. Wanna cum, Daddy.”

“I bet you do, baby.” He braced one hand against the mattress by Derek’s shoulder and grabbed the base of his cock, guiding it to Derek’s hairy globes and spearing it between them and pushing it into Derek’s wet heat. Stiles groaned as he bottomed out. “I’m so not gonna last,” he gasped, leaning down and panting against the back of Derek’s neck.

“Move, Daddy.”

“Wait, wait, wait,” Stiles said, swatting at Derek’s shoulder. “Just wait.”

“Wanna  _ cum _ ,” Derek whined.

“You and me both, big guy.” Derek started shifting forward and back. Stiles smacked him. “No.” After several more seconds of Derek’s whining, Stiles pulled out and flopped to the side, shifting till his back was slightly propped up by a pillow.

Derek turned his head to blearily peer at Stiles. “Daddy?”

Stiles slapped his hips a few times. “Come on, you’re gonna sit on Daddy’s cock. Because you’re gonna work for your orgasm—and mine—but also because you nearly killed me with your monster dick. So.” He pointedly glanced at his own dick that was a fine “basically” six inches, of which, was, in fact,  _ not _ a murderous monster cock. So.

“Daddy,” he whined petulantly.

Stiles gave Derek a vaguely threatening look. “If you wanna cum, you’re gonna sit on Daddy’s dick.”

Derek grumbled and got up on shaky limbs. “You’re never going near my prostate again,” Derek said as he crawled over and straddled Stiles’ abdomen.

“Yes, I am,” Stiles said. “Now, grab Daddy’s cock and impale your puffy little hole.” He smacked Derek’s thigh lightly.

“Daddy,” Derek complained, his cheeks flushing.

“Now you get all shy when  _ I _ say something obscene?” He smacked his thigh again. “Come on, baby, you said you wanted Daddy’s cum inside you. Don’t you wanna cum on my cock?”

“Yes, Daddy.” Derek grabbed Stiles’ length and stroked a few times before positioning it at his entrance and then he was sinking down and lower until he was fully seated with his eyes shut tight, his brow’s pinched in discomfort, and his cheeks flushed prettily with his mouth parted, panting as he got used to the feeling of Stiles inside of him.

“Gonna move any time s— _ oon _ ,” he moaned out, glaring at Derek. “Asshole,” he admonished.

Derek clenched experimentally around Stiles’ member again, leaving Stiles’ rutting up into the tight heat and then Derek was panting, hands braced on Stiles’ headboard. Then he lifted himself up and slowly sucked Stiles back inside of his hole, breathing heavy and eyes half-lidded, his movements slow and exploratory. Stiles moaned and clutched at Derek’s leg’s letting the man explore. Though, eventually, Stiles grew impatient and impossibly turned on, teeth digging into his bottom lip as he watched Derek writhe and shudder as he impaled himself on Stiles’ cock again and again.

“Derek, Derek,” Stiles patted at Derek’s thigh. “Get on your back. I just—Daddy wants to fuck you into the goddamn mattress. Now. On your back.” He was growling by the end what with Derek having been edging him the last ten or so minutes. They can go slow in th future, you know, when their married and the kids are away at college. Right now he just wanted to cum.

Derek eased off Stiles’ cock, but then was scrambling off and hurriedly laying on his back and easily spreading his thighs. Stiles crawled over and lifted Derek’s legs so his heels rested at the bottom of his back, then he grabbed his cock and pushed in, bottoming out quickly after with a low moan let out against Derek’s throat. Derek’s hands migrated to Stiles’ shoulder blades and Stiles leaned lifted his head as he began pulling out and thrusting back in with a hard thrust, kissing Derek with everything he had and then panting against his mouth when he couldn’t focus on anything other than Derek’s hole.

In a daze, Stiles frantically reached around Derek’s ass to lift it just that much, and then Derek was wailing and pushing back as Stiles pushed forward, hitting Derek’s prostate. It was only a few more thrusts before Derek was crying out a mix between Stiles and Daddy and Stiles was biting into the base of Derek’s throat and holding on for dear life as spasmed, shuddering as his orgasm crashed through him.

Stiles slumped against Derek and was asleep in a matter of minutes. Derek followed soon after, once Derek had managed to shift them to their sides.

  
  


  
  
  
  
  


Derek proposes with onion rings.

**Author's Note:**

> Thanks for reading and such.


End file.
